An enjoyable trip would be south under the Skyway Bridge and then into the Manatee River. There are several good anchorages near the mouth of the River, at Desoto Point on the south side and across, along the north side of the River (which we prefer). One can also sail up-river to the Green Street Bridge area where there is a nice anchorage across from the Twin Dolphins
marina. There is a very nice restaurant at Twin Dolphins
and a a great cafe--The Riverside Cafe--on the north side of the River at the Regatta
Point marina. If you want to "Rough It", there's several good anchorages in Terra Cia Bay, which is just north of the entrance to the Manatee River (head east from Marker # 70 to Marker TC and then follow the markers religiously from there out as it does get shallow real quick outside of the channel.
You can also head
north from St. Pete to the old Sea Plane basin on the south side of David Island or head
somewhat further up the west channel there to a public marina on the east side of Davis Island about mid-way up; or, all the way up to the basin near the convention center.
In the lower Bay, one can anchor
on the east side of Egmont--depending upon the weather
and we have also anchored on the east side of Anna Maria Island, just south of the fishing
pier although the tidale currents run strongly through there so you need to ensure you've got your anchor well set.
The previously mentioned anchorage between Jewfish Key and Longboat Key is pretty good but the approach can be tough as the shoal on the south side of Jewfish has really built up. Also, if I were going there I would not go out the southwest channel only to have to come back through the Longboat Key Channel and the bridge. That approach is narrow and frequently loaded with power boaters that have little knowledge of, or care for, rules of the road. Moreover, the current
through that cut can be quite strong unless one hits it at or near slack water
. I'd suggest the ICW from the lower bay. The water's not bad and the two bridges--at Anna Maria and Cortez--open every 30 minutes on the hour.
If you have not done so, I suggest you consider joining one of the local yacht clubs which will allow you to visit many areas very inexpensively as one's first night at reciprocating clubs is free--except for power--and most have good facilities. Normally food
and drink are less costly at YC's as well.